One of his first titles was the punk zine Noise Noise Noise. It was published in Anchorage Alaska from 1994 till 1996. Eleven issues were released during those years.

His next zine, Twenty-Four Hours was begun while he lived in Japan and continued upon his relocation to Austin, Texas, and finally, New York City. This literary zine has featured fiction, interviews, comics and poetry, with contributions from fellow zine makers such as Ben Brown, Tim Doyle and Ben Snakepit. The zine was released in print from 2001 till 2004. Medsker then took the zine online, where it remains. His most current zine is Teach, an autobiographical comic about his life as a teacher and writer in New York City, which he's published since the summer of 2009.

In 2003, Josh Medsker, with the help of Zach Vowell, founded the Austin Zine Library. It consisted of 4,000 to 5, 000 titles. He handed the reins over to Cheetara Thundercats upon his departure for New York City.

Josh Medsker has written for a number of publications, such as Maximum Rock 'N' Roll, the San Francisco Bay Guardian, Anchorage Press, andFriction.